iTunes info: ver. 10.1.0.54 / 23170 songs in my library / 16504 songs within the 105 playlists I have (and which I usually sync with the ipod)

iPod: Classic 120GB (the first 120 GB version that was released)

I came to realize the existence of the problem recently, when I expanded the playlists within the iPod, and of course when sometime I got to see that some playlists on the ipod had fewer songs than the ones on iTunes.

I tried several things, and before everything else I tried with a different iPod, thinking that my iPod 120GB classic was to blame.Still my efforts with my iPhone and another 160BG ipod classic reproduced the same or similar results... So after that I concluded that the problems lies at the iTunes app. Here is a list of what I have tried so far, with no clear result and most definitely with no resolution:

- Made sure I have the latest iTunes app.

- Tried other devices, like my iPhone and a second iPod Classic

- For a minute I was thinking that maybe one of my Hard disks were to blame... but in the long term I realized that it has nothing to do with the HDD that the songs not transferring were stored into.

- Tried new cables

- Uninstalled iTunes and in installed it again while keeping my library intact

- Removed everything regarding Apple from my PC + deleting the whole library. Then installed a fresh copy of iTunes and imported the backup of my library. I then realized that my library .xml file backup was missing several dozens of songs! I was lucky I had also kept a .txt backup for each of my playlists!

- So I deleted again my library and I imported every single playlist from the .txt files, one at a time.

- I then tried to see if the issue had anything to do with my P55 Intel mainboard chip. As some of you may know, a few months back it was reported that the Intel P55 mainboard chips had sync issues with Windows 7 (mostly 64 bit). Actually the issues reported said that iTunes would not sync at all... In my case, iTunes trasfers the songs to my iPod, but not all of them...So I made sure that I had the latest Bios for my mainboard, I also enabled C State at my Bios. Same results...

Some really important notes:

There are songs that sometimes will sync to my iPod and other times they won't ! Strange, huh ?

All my songs are MP3s with the exceptions of a few that are .wav. These few that are .wav never had a problem syncing nor the do now. The problematic songs are some of the .mp3 type.

A lot of the songs in my library (playlists, etc) are VBR mp3s. Some of the songs that are not transfered to my iPod are VBR. Still, this is not a helpful conclusion because other VBR songs sync with no problem at all.

I also saw that some of the songs that cannot be transfered seem to have a specific issue: when I right click on them, on iTunes, the GET INFO panel is grayed out, so I cannot edit it !!! I'm also not able to do other things like "convert ID3 tags", etc. When I try to do this, I get the message: "Could not convert ID3 tags. The song may be write-protected or of the wrong type"So, I go to my HDD onto the folder I have this song, and I right click on it (on windows explorer) to see the permissions and the attributes. The songs are NOT read-only... and the permissions are exactly the same as of the songs that have no problems being synced by iTunes....

However, what I did for these songs, was that I right clicked on them and chose: "Create MP3 version". So I exchanged the old problematic (for iTunes) version with the new versions (made by iTunes) and the problem seems to be fixed. Now the songs are editable in iTunes and of course they CAN be synced properly to the iPod.

And most important: There are also other songs (that can't be synced) that do not have the above mentioned issues. So I can edit their INFO on iTunes, I can convert the ID3 tags, they are of the proper kind / type (mp3) but they still cannot be synced to my iPod... And this is what bugs me.

Hypothetically, the above mentioned solution (apply "create MP3 version" via iTunes) to all the problematic songs would probably resolve the "won't sync" issue, but as you understand in a library of so many thousands of songs, it is not the most efficient....

This is what I have tried so far.For me it seems that iTunes has several issues that have to be resolved.I have a huge library of songs and for years now I have organized it with iTunes.I listen to my iPod on daily basis and Apple has to provide a solution about this matter. Going through every single song (that won't sync) and creating an "iTunes-preferred" MP3 version of it... (although they already are Mp3s) is not an efficient solution for huge libraries as the one I have.

I myself have not had and I don't know if I'll ever have in the future the time to do this... for each song

- Most of the problematic songs (if not all) are stored in an internal HDD. The problems occured when I recently upgraded to win 7 from win XP.

- I have noticed that even when I remove the READ-ONLY status from the properties of the folders... if I right click -> properties I can see again the Read-Only status !! Maybe because I'm not the owner (as you suggested) ??

- The above mentioned HDD seems to have an owner that is not me... probably a remain from windows XP (?).

- Changing the permissions to Full control for those folders/files/songs that had the issue helped a bit: Now these songs' Get Info is not greyed out !! when I right click on them on iTunes. BUT: some of them seem to sync now, other still won't !!

So what I'm gonna do now is follow these steps and give feedback:

1) Take Ownership of the folders/files...2) Change the permissions of those folders to Full Control for the user I login with on my windows 73) Uncheck (again) the Read-Only status on those folders...

I compare the songs included there, with the ones included at the corresponding playlist that is synced to the iPod.

The iTunes playlist has 650 songsThe same playlist in iPod has 649 songs...

I was able to find which song was not synced to the iPod...So I go and "Create and MP3 version" of that song. I re-sync the iPod.Result: now, that particular song has been transfered/synced to iPod, but the iPod playlist has now only 648 songs... which means that 2 other songs failed to sync !!!

As I said above after taking care of the permissions of the songs, and successfully making them editable on iTunes, some of them will now sync and some of them won't.

One partial solution is to find the songs that won't sync (which is really difficult when you have playlists of hundreds of songs) and create a new MP3 version with iTunes.

Now I', experimenting on something else... I edit those songs via iTunes and I add/change something on their tags, for example I type a composer, or the year field, etc.I have tried this with 3 songs and it seems - so far- to work..! These ID tag changes seem to "wake up" iTunes and after a new synch, these songs seem to sync to iPod!Now I don't want to sound too enthusiastic about this, because there is a chance this will happen only for a few songs.. as every other solution I tried... above.

I will report back when I have more songs edited and -hopefully- synced to my iPod by editing the ID tags...

I had playlists of aprox. 350 songs (each one) in iTunes, and after the sync, there were only like 287 songs of them on iPod (at that specific playlist).

Instead of going through every un-synced song, I selected all the songs in the specific iTunes playlist with the purpose to edit the ID3 Tags, and see if they would then be synced.. to iPod

I did not want to change important tags such as artist, name, album, etc...So what I did was that I selected all the songs within the playlist and I edited the (pretty useless) "Comment" tag field. So it was like editing simultaneously the comment of all those songs, and I wrote whatever non sense I wanted there (e.g. rock music, or just pressed two spaces...).This way, all the songs of that playlist were now having a newly edited tag.On the next Sync.. all the songs were transfered successfully to iPod !!

Yay! This means success!

Let's hope this lasts.... and no fresh terrifying sync issues will come up in the near future...

That is so VERY odd that rewriting the tags let them sync, but whatever works!Well done on discovering that!I do use the Comment field, also the Grouping field, but if this happens to me I will use the Sorting field on the Options tab.

Last night I had a few songs say they would not be synced because they couldn't be found. When I did a Get Info, itunes found them OK. And, they did sync to the ipod.Yikes.

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